Sodium borohydride → 3-Bromo4-(N,N-dimethylsulfamoyl)benzyl alcohol

Participants

Reaction Steps

To a solution of OBS02001 (6.0 g, 19.47 mmol) in anhydrous THF (50 mL) was added sodium borohydride (0.81 g, 21.42 mmol). The mixture was stirred at room temperature for 4 h, quenched with water (CARE!!) and filtered through a Celite pad. The filtrate was concentrated in vacuo and re-dissolved in DCM (200 mL). The organic layer was washed with brine (2×200 mL), dried (Na2SO4) and filtered. Concentration in vacuo of the filtrates gave OBS02002 as a pale yellow oil (5.54 g, 92%). TLC [SiO2, EtOAc-n-hexane (1:1)] RF=0.47; 1H-NMR (270 MHz, CDCl3)=2.97 (6H, s), 3.14 (1H, bs, OH), 4.51 (2H, s) 7.19 (1H, dd, J=1.5, 8.1), 7.37 (1H, d, J=8.4), 7.52 (1H, d, J=1.8).

Provenance & Evidence